Polyether-substituted glycidyl ethers



United States Patent POLYETHER-SUBSTHTUTED GLYCMYL ETHERS Van Pt.Gaertner, Dayton, Ohio, assignor to Monsanto (Ihemical Company, St,Louis, Mo., a corporation of Delaware No Drawing. Filed Sept. 30, 1959,fier. No. 843,353

4 Claims. (61. 269-348) This invention relates to the ether-substitutedglycidyl ethers. In one aspect, this invention relates toalkoxyalkenoxyand alkaroXyalkenoxy-, as well as alkoxypolyalkenoxyandalkaroxypolyalkenoxy-1,2-epoxypropanes as new compounds. In anotheraspect, this invention relates to alkoxyalkenoxyand alkaroXyaJkenoXy-,as well as alkoxypolyalkenoxyand alkaroxyalkenoxy-,hydroxypropanesulfonates as new compounds. In another aspect, thisinvention relates to methods for preparing said polyether-substitutedglycidyl ethers from an alcohol and an epoxyalkane. In another aspect,this invention relates to new surfactant compositions which are highlyresistant to curd-forming metal cations of hard water. In anotheraspect, this invention relates to methods for increasing the lime soapdispersant efiiciency of detergent compositions.

It is generally Well known that soaps, e.=g., the sodium, potassium andammonium salts of fatty acids, precipitate as insoluble fatty acidsalts, more commonly referred to as lime soaps, in hard water or otherwater containing polyvalent metal ions such as calcium and magnesiumions. Such precipitated lime soaps have a tendency to coagulate and formundesirable curds, scums, films or deposits which are observed in theWash stand and bathtub and which stick to the clothes during the rinsingoperation, thereby giving the clothes an unsightly, dingy appearance anda rancid odor. The formation of insoluble limesoaps also destroys orreduces the foaming and cleansing power of the soap. i

It is also generally well known that surfactant compositions are usefulin dispersing lime soap and thereby preventing the formation ofundesirable curds, scurns and the like. Such surfactant compoundsusually comprise a molecule having hydrophobic as Well as hydrophilicgroups. Although a few compounds which are fairly insoluble in water areknown to have good lime, soap dispersant properties, very solublecompounds usually do not possess good surface active properties and arenot good surfactants. Therefore, it is necessary to develop compoundswhich have the proper balance of hydrophobic and hydrophilic groups inorder to prepare improved surfactants.

An object of this invention is to provide alkoxyalkenoxyandalkaroXyalkenoXy-, including alkoxypolya-lkenoxy andalkaroxypolyalkenoxyepoxypropanes as new compounds.

Another object of this invention is to provide alkoxyalkenoxy-, andalkaroxyalkenoxy-, including alkoxypolyalkenoXy-, andalkaroxypolyalkenoxyhydroxypropanesulfonates as new compounds.

Another object of this invention is to provide methods for preparingpolyether-substituted glycidyl others from an alcohol and anepoxyalkane.

Another object of this invention is to provide new allpurpose soapcompositions which form little or no insoluble lime soap curd when usedwith hard water.

Another object of this invention is to provide new surfactantcompositions which are highly resistant to curd-forming ingredients ofhard water.

Another object of this invention is to provide a method for increasingthe lime soap dispersant eihciency of soapcontaining detergentcompositions to reduce the coagulation of precipitated lime soap in hardWater and there- Patented Sept. 3, W63

ice

by prevent the formation of curd, scurns, deposits, films and the like.i

Other aspects, objects and advantages of this invention will be apparentfrom a consideration of the accompanying disclosure and the appendedclaims.

In accordance with this invention, a long-chain monohydric alcohol isalkenoxylated in a two step process with at least an equimolar amount,and preferably an excess of an epoxyalkane and then with a.substantially equimolar amount of epichlorohydrin to form apolyether-substituted chlorohydrin as illustrated by the fo lowingequations:

RO[OH2CHO]XCH2CHCHZCI 1'1 11 wherein R is a radical selected from thegroup consisting of alkyl and alkaryl radicals having from 8 to 24carbon atoms, R is a radical selected from the group consisting ofhydrogen and lower alkyl radicals, each of said R being the same ordifierent when x is greater than 1, and x is a Whole number less than10. The polyether-substituted chlorohydrin is then dehydrochlo rinatedto a polyether-substituted glycidyl other as illustrated by thefollowing equation:

wherein R, R, and x are as above defined.

Further, in accordance with the present invention, there are provided,as new compounds, polyether-substituted hydroxypropanesulfonates of theformula RO-[CH2(}1HO]r-CH2)CHOH2SO3Z R on wherein R, R, x and Z are asabove defined.

Further, in accordance with the present invention, there are providednew surface active compositions comprising, as the active ingredient, apolyether-substituted hydroxypropanesulfonate of the formula givenabove.

.Further, in accordance with the present invention, there are providednew all-purpose detergent compositions comprising a sodium, potassium orammonium salt of a longsclrain fatty acid, and, as an essentialingredient, a polyether-substituted hydroxypropanesulfonate of -theformula given above.

Further, in accordance with the present invention, there are providedmethods for increasing the lime soap dispersant efficiency ofsoap-contm'ning detergent compositions by adding a polyether-substimtedhydroxypropanesulfonate of the formula given above to a sodium,potassium or ammonium long-chain fatty acid soap.

The monohydric alcohols used in the reaction of the present inventionare preferably the long 'chain alcohols and alkylphenols having at leasta total of 8 carbon atoms per molecule. These alcohols may contain asmany as 24 carbon atoms per molecule in either a straight-chain or abranched-chain arrangement and may be unsaturated. The alkylphenols may1 so include the monoalkylated as well as the polyalkylated arylradicals.

Illustrative examples of some alcohols which can be used include theZ-ethylhexyl, ison'onyl, n-dodecyl, tertdodecyl, 2-propylheptyl,S-ethylnonyl, 2-.butyloctyl, ntetradecyl, n-pentadecyl, tert-octadecyl,2,6,8-trimethylnonyl, and 7-ethyl-2-methy1-4-undecyl alcohols.

'An especially valuable class of alcohols which are use- 111 for thepreparation of the presently provided new compounds of my inventioninclude the branched chain alcohol wherein the alkyl radical is derivedfrom an olefin monomer, dimer, trimer, tetramer, pentamer, or the like,carbon monoxide, and hydrogen according to the Oxo process. Suchalcohols include the branchedchain tridecyl alcohol derived frompropylene tetramer or butylene trimer, carbon monoxide and hydrogen;branched-chain decyl alcohol prepared from propylene trimer, carbonmonoxide and hydrogen; branched-chain hexadecyl alcohol prepared frompropylene pentamer, carbon monoxide, and hydrogen; and branchedechain Inonyl alcohol prepared from diisobutylene, carbon monoxide and hydrogen.

Illustrative examples of some alkylphenols which can be employed asreactants in this invention include tertoctylphenol, nonylphenol,(2-ethylheptyl)phenol, decylphenol, 4-tert-dodecylphenol,Z-tn'decylphenol, 3-tertoctadecylphenol, 2-nonyl-1-naphthol), 1-(2-butyloctyl)- Z-naphthol, 2,4-dirnethylphenol, 3-butylphenol, and 2,4-dinonylphenol.

The epoxyalkane reactant used in the reaction of this invention can beany epoxyalkane having a terminal group; i.e., an epoxyalkane having thestructure wherein R is selected from the group consisting of hydrogenand lower alkyl radicals. Preferably, the alkyl radical contains lessthan 6 cazobon atoms and may have either straight chain orbranched-chain configuration. Such alkyl radicals include methyl, ethyl,propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, isohexyl, tertbutyl,Z-methylbutyl, 2,2-dimethylpropyl, and 2-methylpentyl.

Illustrative examples of some epoxyalkanes which can be used intheprocess of this invention include ethylene oxide, 1,2-ep10xypropane(propylene oxide), 1,2-epoxybutane, 1,2-epoxypentane, 1,2-epoxyhexane,1,2-epoxyheptane, l,2-epoxyoctane, 3-methyl-1,2-epoxybutane, 4-methyl-1,2-epoxypentane, and 4,4-dimethyl-1,2-epoxypentane.

The product of the first alkenoxylation step is an alkoxyalkenoxyalkanolor an alkaronyalkenoxyalkanol, including an alkoxypolyalkenoxyalkanol oran alkaroxypolyalkenoxyalkanol, having from 1 to as many as 10 alkenoxygroups in the molecule depending upon the number of moles of theepoxyalkane reactant used. Thus, using 1 mole of the epoxyalkanereactantand an alcohol, the product is an alkoxymonoalkenoxyalkanol whereasusing 2 moles of the epoxyalhane and 1 mole of the alkyl alcohol gives aproduct of alkoxydi(alkenoxy)- alkanol. Ordinarily, the major product ofthe alkenoxylation step has the structure shown inEquation 1 with thealkyl group identified by R attached to the carbon atom adjacent theoxygen atom of the alkenoxy group. However, this reaction usuallyresults in the formation of somealkoxyalkenoxyalkanol or somealkaroxyalkenoxyalkanol products of the structure wherein the alkylgroup identified by R is attached to a in the 2 position .and it isintended that the alkenoxy group cover both isomers.

The first alkenoxylation step is preferably conducted in the presence ofa catalyst which can be either an alkaline type catalyst or an acid typecatalyst. Suitable alkaline type catalysts include the alkali metaloxides,

hydroxides, carbonates, borates, and the like which are alkalinereacting. Such catalysts include sodium oxide, potassium oxide, lithiumoxide, sodium hydroxide, p10- tassium hydnoxide, lithium hydroxide,sodium carbonate, potassium carbonate, lithium carbonate, sodiumbicarbonate, sodium borate, potassium bonate and the like. Suitable acidtype catalysts include sulfuric acid, alkanesulfonic acids, arylsulfonicacids, and Lewis acids. The Lewis type acids include aluminum chloride,boron trifluoride, stannic chloride, ferric chloride, and the like.Boron trifluoride-etherate is a preferred catalyst of this type.Although either the alkaline or the acid type catalyst can be used inthe first alkenoxylation step, it is usually preferred to use thealkaline type catalyst.

The amount of the catalyst present in the first alkenoxylation step canbe varied over wide limits as determined by the particular epoxyalkanereactant used, by the temperature desired, and by the reaction timeselected. Ordinarily, theamount of catalyst will be between about 0.1%

and 5.0% by weight of the amount of the alcohol reactant present.

Ordinarily, the first alkenoxylation reaction is carried out at atemperature in the range of from 50 C. to 160 C.; however, thetemperature selected depends to a considerable extent upon the nature ofthe catalyst employed. Thus, it is usually sufiicient to use atemperature in the range of from 50 C. to C. when using an acid-typecatalyst Whereas a temperature in the range of from 100 C. to C. willusually be employed with an alkaline type catalyst. lower molecularweight epoxyalkanes usually requires the use of the alkaline-typecatalyst and, therefore, a temperature in the range of 100-160 C. Incomparison, alkenoxylation of the alcohol with the higher molecularweight epoxyalkanes may require the use of an acid-type catalyst, andtherefore a temperature below 100 C. Alkenoxylation using the lowermolecular epoxyalkanes can also be conducted using an acid-typecatalyst; however, a temperature in the lower portion of the range mustbe used in order to minimize the formation of by-products.

The first alkenoxylation reaction may be carried out at substantiallyatmospheric pressure although elevated pressures can also be usedadvantageously.

The reaction of the alcohol with the epoxyalkane is primarily anaddition-type reaction resulting in the formation of a single product.But some reaction conditions may result in the formation of by-products,necessitating a separation step. Thus, some ketone by-products may beformed in the reaction requiring removal by distillation. The presenceof water in the alkenoylation step results in the formation of glycolbut the formation of this by-product can be reduced by dehydrating thealcohol reactant before conducting the reaction. If an alkaline-Alkenoxylation of the alcohol with the type catalyst is used in thefirst alkenoxylation step, this catalyst must be removed beforeconducting the second alkenoxylation step using epichlorohydrin. Thisalkaline catalyst is best removed from the alkoxyalkenoxyalkanol productby Washing with water. It is not necessary to remove an acid-typecatalyst used in the first step of the alkenoxylation reaction sincethis same catalyst can be used in the second alkenoxylation step withepichlorohydrin.

The second alkenoxylation reaction step using epichlorohydrin isconducted using substantially only 1 mole of epichlorohydrin per mole ofthe alcohol reactant used in the first alkenoxylation step. The use ofmore than 1 mole of epichlorohydrin results in the formation of apolyglyceryl ether substituted with a number of chloromethyl groupswhich would then be converted into polysulfonate groups in thesubsequent sulfonation. This second alkenoxylation step differs from thefirst alkenoxylation step in that the alkenoxylating reactant is achloro-substituted epoxyalkane instead of an alkyl-substitutedepoxyalkane as in the first step and substantially only 1 mole of theepoxyalkane per mole of alcohol is used in the second step whereas morethan 1 mole of the epoxyalkane can be used in the first step. As used inthis specification, substantially 1 mole is defined as being one orslightly more than 1 mole and always less than 2 moles; that is,substantially 1 mole can be as much as 1.25 or 1.3 moles. In conductingthe second alkenoxylation reaction, it is preferred to use at least 1mole of the epichlorohydrin per mole of the alcohol reactant, and veryoften as much as 1.2 moles, in order to insure completechlonoalkenoxylation of the alkoxyalkenoxyalkanol product produced inthe first alkenoxylation step. The presence of unreactedalkoxyalkenoxyalkanol in the final product is not desirable since it isdetrimental to surfactancy and not readily separated from the desiredproduct.

The second alkenoxylation step using epichlorohydrin is conducted in thepresence of a catalyst. This catalyst can be any of the acid-typecatalysts used in the first alkenoxylation step but the alkaline-typecatalysts can not be used. A preferred catalyst is boron trifiuoride. Asin the first alkenoxylation step, the amount of catalyst used willusually amount to 0.1% to 5% by weight of the amount of alcohol reactantused. As noted previously, if an acid catalyst is used in the firstalkenoxylation step, additional catalyst will not be necessary in thesecond alkenoxylation step except to replace any catalyst which may havebeen lost.

The second alkenoxylation step can be carried out at room temperature;however, usually elevated temperatures are employed in order to shortenreaction times. Ordinarily, the temperature will be maintained at lessthan 140 C. A preferred temperature range is from 60 C. to 120 C. Thetemperature is dependent to some extent upon the nature of the catalystused; less active catalysts requiring higher temperatures. Thus, borontriiluoride acts as a very reactive catalyst in this step so thatusually the temperature is maintained below 100 C.

As in the first alkenoxylation step, the pressure is ordinarilymaintained at substantially atmospheric pressure in the second stepalthough elevated pressures can be employed.

The product from the second alkenoxylation step is primarily apolyether-substituted chlorohydrin, more specifically an1-alkoxyalkenoxy-3-chloro-2-propanol,l-alkaroxyalkenoxy-3-chloro-2-propanol, l-alkoxypolyalkenoxy-3-chloro-2-propanol, or 1-alkaroxypolyalkenoxy-3-chloro- Z-propanol, asshown in reaction 2.

The second alkenoxylation reaction is primarily one of addition so thatusually there are very few other products to be found in the reactionproduct.

Formation of the glycidyl ethers according to the invention, as shown inEquation 3 above, takes place 6 readily by contacting thepolyether-substituted chlorohydrin produced in the second alkenoxylationstep with an aqueous alkaline solution. This reaction involvesdehydrochlorination of the chlorohydrin to form the epoxy group. Thealkaline solution may be an aqueous solution of an alkali metalhydroxide or a basically reacting salt thereof, e.g., sodium hydroxide,potassium hydroxide, lithium hydroxide, sodium carbonate, potassiumcarbonate, lithium carbonate, sodium acetate and the like. Ammoniumhydroxide or ammonium salts can not be used. Advantageously, thedehydrochdorination reaction is carried out in a solvent media in orderto obtain suitable reaction times and complete dehydroohlorination. Thesolvent should be one which is soluble in water and suitable solventsmay include aliphatic and aromatic hydrocarbons such as toluene orhexane, others such as isopropyl ether or dioxane and the diallkylsulfoxides. The diallkyl suifoxides are preferred solvents and are thosein which there are present from 1 to 5 carbon atoms in each alkylradical e.g., diniethyl sulfoxide, diethyl sulfoxide, dipropylsulfoxide, di-n-butyl sulfoxide, di-tert-amyl sulfoxide, ethylmethyisultfoxide, n-amyl-n-propyl sulfoxide, and the like. The quantity ofdiluent employed depends somewhat upon the nature of the individualchlorohydrin and upon the amount of the alkali hydroxide present. Withrespect to the quantity of sulfoxide, there should be present a quantityof sulioxide which is at least. 10% by weight of the amount of thechlorohydrin and preferably from 25 to by weight of the amount of thechlorohydrin. Adv'antageously, substantially equal amounts of thesuitoxide and the chlorohydrin are employed. A molecular equivalent ofthe alkali metal hydroxide with respect to the chlorohydrin should bepresent and the best results are obtained by employing a slight excessof the hydroxide;

The dehydrochlorination step takes place by contacting the chlorohydrinwith the aqueous alkali hydroxide in the presence of the diluent atordinary or moderately increased temperatures, e.g., at temperatures offrom room temperature to C. External heating need not generally beemployed, although under certain conditions, e.g., when the reaction iseffected in the presence of a dilute aqueous alkali metal hydroxide,external heating may be used.

When the dehydrochlorination reaction has been completed, which can benoted by cessation in changes of refractive index, the glycidyl ether isseparated from the reaction mixture by customary isolation procedures.Byproduct salt may be removed by filtration. Preferabiy, the otherproduct is recovered by solvent extraction, whereby the upper layer isseparated, water washed to remove any residual sait and diluent, andfinally distilled. The lower layer, which comprises most of thesullfoxide and excess alkali can be recycled in a continuous process.Generally, good results are obtained by simply filtering the crudereaction mixture to remove the salt and a1- lowing the filtrate tostratify, whereby the ether product is recovered as the upper layer.Water washing of the upper layer generally gives a satisfactory etherproduct without further purification.

The product of the dehydrochlorination step is a glycidyl other, morespecifically, 3-alkoxyalkenoxy-L2- epoxy-propane,3-alkaroxyaikenoxy-1,2-epoxypropane, 3-alkaroxypolyalkenoxy-l,2-epoxypropane, or3-allroxypolyatlkenoxy-l,2-epoxypropane. There can be several iowerai-kyl radicals identified by R in the formulas when x is greater than1; such as, when x is 2, there are two R groups in the formula. Theselower ailkyi groups can be the same or difierent, including hydrogen.For example, when x is 2, one R can be methyl and the other ethyl, orone can be methyl and the other hydrogen or both can be methyl. Theseproducts are generality mobile to viscous iiquids which vary in colorfrom 7 water-white to amber. Illustrative examples of some of theseglycidyl ethers are as follows:

3 2-tert-octadecyloxyethoxy) -1,2-epoxypropane 3-( 2-nonylphenoxyethoxy)1 ,2-ep oxyprop ane 1 3- 1- (2-propy lheptyloxy) -2-propoxy] 1 ,2-epoxypropane 3 l- (nhexadecyloxy) -2-propoxy] -1 ,2-ep oxypropane 3- 1-(2,4-dinonylphenoxy) -2-butoxy] -l ,2-ep oxypropane 3-[ 1-(n-hexadecyloxy) -2-butoxy] -1,2-epoxypropane 3 1- (n-oetadecyloxy)-2-butoxy] -1,2-epoxypropane 3-{2- [-butyloctyloxyethoxy] ethoxy}- 1,2-epoxypropane 3-{2- [2 (decylphenoxy)ethoxy]ethoxy}-1,2-epoxypro- Ipane 3 {1 [l-(tridecyloxy) 2 propoxy]-2-propoxy}-1,2-

epoxypropane a a 3-{1-.[1-(n-hexadecyloxy) 2 propoxy] -2-p-ropoxy}-1,2-

epoxypropane 'Ilhe glycidyl ethers thus obtained are directly useful fora variety of commercial applications. For example, these glycidyl ethersare excellent solvents for nitrocellulose and, in addition, can be usedas polymerizable solvents in fluid epoxy resin systems. Furthermore, asdisclosed hereinafter, these glycidyl ethers are readily converted uponreaction with an alkali metal sulfite into exceptionally valuablesurfactants having good lime soap dispersion properties.

As shown in Equation 4, the glycidyl ether can be reacted with an alkalimetal sulfite r bisulftte to form an alkali metal salt of thepolyether-substituted 2-hydroxy-l-propanesulfonate and, an alkali metalhydroxide as a by-product. The alkali metal can be selected from thegroup consisting of sodium, potassium, and lithium. If desired, analkaline earth metal sulfite or bisulfite can be used in place of thealkali metal sulfite and when using this reactant, the alkaline earthmetal can be selected from the group consisting of calcium, strontium,barium and magnesium. The reaction of the glycidyl ether with the alkalimetal or alkaline earth metal sulfite or bisulfite is advantageouslyefiected while substantially neutralizing the alkali metal or alkalineearth metal hydroxide as it is formed in the reaction. Thus, to get goodyields of the propanesulfonate it is preferred to neutralize thehydroxide as it is formed by the continuous addition of an acid, such ashydrochloric or sulfuric acid, at a rate so as to maintain the pH of thereaction mixture at from approximately pH 6-8 and definitely below 10when using use as a solvent. The use of water as a solvent withoutadmixture with ethanol requires more elevated temperatures in order toeffect the reaction. Furthermore, the use of water without [admixturewith ethanol generally requires the use of elevated pressures.

The sulfonation reaction can be carried out at temperatures within therange or from 50- C. C. using a water-ethanol solvent. The reaction canalso be carried out at a temperature within the same range using wateras a single solvent but a reaction time of from 2 to 3 'days will berequired unless a temperature of C. is used when the reaction time willbe 1 to 2 hours.

The sulfonation reaction can be carried out at atmospheric pressure 'orsubstantially atmospheric pressure when using a water-ethanol solvent.However, if water is used as a single solvent superatmospheric pressurewill be required in order to eliect the reaction in reasonable periods.

When the addition reaction has been completed, the sulf-onate product isreadily recovered by customarily employed isolating procedures. Aproduct of good purity is obtained by removing the Water in the reactionmixture by azeotropic distillation using a suitable azeotropeformer suchas isopropanol. The inorganic salts present in the reaction mixture areinsoluble in hot isopropanol and, since the sulfonate is substantiallysoluble therein, the salts may be removed by filtration. It is usuallydesirable to have a small amount of water present in the mixture to hefiltered, particularly with the higher molecular weight sulfonateproducts, in order to prevent any of the sulfonate product fromprecipitating out of solution. The sulfonate product is then recoveredfrom the isopropanol solution by volatilization of the solvent.

An alternative method for forming the polyether-substitutedZ-hydroxy-l-propanesulfonate product of this invention involvestreatment of the polyether-substituted chlorohydrin obtained from thesecond alkenoxylation step with epichlorohydrin directly 'with theallnali metal sulfite or bisulfite. This method requires the use ofelevated pressures and temperatures, usually in the'range of ISO-210 C.,and somewhat longer reactiontimes in order to eliect conversion to thealkali metal sulfonate. This method is less preferred than the methodinvolving formation of the glycidy-l ether.

The sulfonate product of this invention, as shown in Equation 4, is an3-(alkoxyalkenoxy)-2-hydroxy-1-propanesulfonate salt or an 3(alkaroxyalkenoxW-Z-hydroxy-l-propanesulfonate salt and, where an excessof the epoxyalkane was employed in the first alkenoxylation step, theproduct is an 3-( alkoxypolyalkencxy)-2-hydroxy-l-propanesulfonate saltor an S-(alkaroxypolyalkenoxy)-2-hydroxy-l-propanesultonate salt.Illustrative examples of some of the sulfonate products of thisinvention are as follows:

Sodium, potassium or lithium3-(2-tert-octadecyloxyethoxy)-2-hydroxy-1-propanesulfonate Sodium,potassium or lithium 3-(2-nonylphenoxyethoxy)-2-hydroxy-l-propanesulfonate Sodium, potassium or lithium3-[1-(2-propylheptyloxy)- Z-propoxy] -2-hydroxy-1-prop ane sulfonateSodium, potassium or lithium 3-[l-(n-hexadecyloxy)-2- prop oxy]-2-hydroxyl-propane sulfonate Sodium, potassium or lithium3-[l-(2,4-dinonylphenoxy)- Z-butoxy] -2-hydroxyl-propanesulfonateSodium, potassium, or lithium 3-[1-(n-hexadecyloxy)-2- butoxy]-2-hydroxy-'1 -prop anesulfon ate Sodium, potassium or lithium3-[l-(n-octadecyloxy)-2- butoxy]-2-hydroxy-l-propanesulfonate Sodium,potassium or lithium 3% 2-[2-(2-butylocty1oxy)- ethoxy] -ethoxy}--2-hydroxyl-propanesulfonate Sodium, potassium or lithium 3%Z-[Z-(decylphenoxy) ethoxy] ethoxy }-2-hydroxy-l-propanesulfonatebleaching, and the like.

Sodium, potassium or lithium 3% 1-[1-( tridecyloxy)-2- propoxy]-2-propoxy }-2-hydroxy-l-propanesulfonate Sodium, potassium or lithium3% 1-[1-(n-hexadecyloxy)- Z-prop oxy] -2-propoxy}-2-hydroxyl-propanesulfonate Sodium, potassium or lithium 3% 1%1-[(2-ethylheptyl)- phenoxy] 2 hexoxy} 2 hexoxy}-2-hydroxy-1-propanesulfonate Sodium, potassium or lithium 3 {1 [1(lauryloxy)-2- butoxy] -2-bwtoxy }2-hydroxy- 1 -propanesul-fonateSodium, potassium or lithium 3% 2% 2-[2-(2-ethylhexyloxy)ethoxy] -ethoxyiethoxy} 2 hydroxy-lpropaneisulfonate Sodium, potassium or lithium 3% 2%2-[2-(4-tert-dodecylphenoxy)]-ethoxy ethoxy} 2hydroxy-l-propanesulfonate Sodium, potassium or lithium 3 {1 [1(nonyloXy)-2- prop oxy] -2-butoxy }-2-hydroxyl-propanesulfonate Sodium,potassium or lithium 3-(1-tertdodecy1oxytri-2- propenoxy) -2 -hydroxy- 1-propane suit on ate Sodium, potassium or lithium3-(l-tert-dodecyloxytri-Z- butenoxy) -2-hydroxyl-propanesulfonateSodium, potassium or lithium 3-(1-isononyloxyhexa-2- ethenoxy) -2-hydroxy- 1 -pro pane sulf onate Sodium, potassium or lithium3-[l1-(2-tridecylphen0xy)- :hexa-Z-ethenoxy] -2-hydroxy-1 propanesulfonate Sodium, potassium or lithium 3-(l-n-pentadecyloxyhexa-Z-pentenoxy) -2-hydroxyl-propanesulfonate Sodium, potassium :or lithium3-[1-(3-butylphenoxy)- hexa-2-propenoxy1 -2-hydroxyl-propanesulfonateSodium, potassium or lithium 3-(1-isodecyloxyhexa-2- propenoxy)-2-hydroxyl-propanesulfonate The sulfonate products of this inventionare stable, usually water soluble, firiable solids or viscous gums. Theyare valuable articles of commercial interest and have many varied uses,particularly as surface active agents. They can be used as wetting,frothing or washing agents in the treatment and processing of textiles,for dyeing, for pasting of dyestuffs, fulling, sizing, impregnating andIn addition, these compounds are useful for preparing foam in fireextinguishers, for use as froth flotation agents, as air entrainingagents for concrete or cement, and as aids in the preparation of otherarticles of commerce. These sulfonate compounds are particularly usefulin soap and synthetic detergent compositions as lime soap dispersants.

The advantages, the desirability and usefulness of the present inventionwill be illustrated by the following examples.

Example 1 In this example, 3-[1-(n=hexadecyloxy)-2-propoxy]- 1,2epoxypropane, and sodium 3-[l-(n-hexadecyloxy)-2-propoxy]-2-hydroxypropanesulfonate were prepared from substantially 1mole of propylene oxide and 1.2 moles of epichlorohydrin. Cetyl alcoholwas dried by heating and stirring in a suitable vessel 242 g. (1.0 mole)of cetyl alcohol for a period of 2 hours at a temperature ofapproximately 60 C. in a nitrogen stream. Then 2.3 g. of potassium metalwas added. After dissolution of the potassium in the cetyl alcohol, 87g. (1.5 moles) of propylene oxide was added dropwise during a period oftwo hours, during which time the temperature was increased from 90 C. to150 C. After completion of the reaction, the reaction mixture was cooledto approximately 100 C. and the catalyst neutralized using Dry Ice and:water. Thereafter, the reaction product was dried over anhydrous sodiumsulfate. After standing overnight, the drying agent was filtered oif andthe filter cake washed with hexane. The filtrate was distilled to obtaina 114.9 g. traction boiling at 0.3 mm. between 144 C. and 161 C. Thisproduct is mainly l-n-hcxadecyloxy-Z-propanol and was found to have acarbon and hydrogen analysis of 75.70 wt. percent carbon and 13.39 wt.percent hydrogen as compared with calculated 10 values of 76.0 wt.percent carbon and 13.4 wt. percent hydrogen.

The second alkenoxylation step was carried out by heating 113 g. (0.376mole) of the 1-n hexadecyloxy-2- propanol with 41.6 g. (0.45 mole) ofepichlorohydrin using 1. 0 ml. boron trifiuoride d-iethyl ether complex(47% BF as a catalyst. The reaction temperature was maintained at 90 C.by regulating the :rate of addition of the epichlorohydrin. After theaddition of epichlorohydrin was completed, the reaction mixture washeated for an additional one hour while maintaining the temperature atC. The product of this reaction, 1- (1n-hexadecyloxy-Z-propoxy)-3-chloro-2.-propanol, was not separated fromthe reaction mixture but was dehydrochlorinated in the next step to formthe glycidyl ether.

In the dehydrochlorinating step, 50 g. (0.50 mole) of 40% sodiumhydroxide and 50 ml. of water were added to the above reaction mixtureto which was also added ml. of dimethyl sulfoxide. This mixture was thenheated at a temperature of 90 C. for a period of 1.5 hours. The hotreaction mixture was then filtered to remove the sodium chloride formedin the reaction and the oily layer was washed twice with hot saturatedaqueous sodium chloride solution in the presence of hexane. The oil wasdried over sodium sulfate and the hexane was removed by evaporationunder reduced pressure to obtain a faintly yellow oil which is theglycidyl ether, 3- 1- n-hexadecyloxy -2-propoxy] 1 ,Z-epoxypropane Thesodium hydroxy snlfonate product was formed by heating 53.5 g. (0.15mole) of the glycidyl ether obtained in the above dehydrochlorinationstep with 25.2 g. (0.20 mole) of sodium sulfite in 100 ml. of ethanolmixed with 100 m1. of water. The pH of the solution was maintained at pH7-9 by the periodic addition of 6 N hydrochloric acid. The heating wascontinued for a period of 10.5 hours while maintaining the temperatureat 80 C. At the end of this time, the reaction mixture was dried bystripping ofi the water under reduced pressure while replacing it withisopropanol. The hot isopropanol solution was then filtered to removeinsoluble material :and the hot filtrate cooled to crystallize out thesulfonate product which was recovered by filtration. The recoveredproduct was dried in an oven at a temperature of 45 C. to obtain 39 g.of the desired sodium 3-[1-(n hexadecy-loxy) 2 propoxy] 2hydroxy-l-propanesulfonate which is substantially white in color.

Example 2 In Example 1 a fraction boiling from 166 C. to 205 C. at 0.3mm. (mainly from 182 to 197 C.) is the product resulting from thereaction of 1 mole of the cetyl alcohol with 2 moles of propylene oxide,identified as 1-(ln hexadecyloxy 2 propoxy)-2-propanol. It contained73.67% C. and 13.10% H; the calculated values are 73.7 and 12.9,respectively. Then, in the second alkenoxylation step, 95.5 g. (0.266mole) of the above reaction product was heated with 29.6 g. (0.319 mole)of epichlorohydrin using 1.0 ml. of boron trifluoride-diethyl ethercomplex as a catalyst. The epichlorohydrin was added over a period of 30minutes at a rate to maintain the temperature at approximately 85 C.After the addition of all the epichlorohydrin, the heating was continuedfor a period of 1 hour at 8590 C. The reaction product, 1% 1- E 1-(n-hexadecyloxy) -2-propoxy] -2.-propoxy }-3- chloro-Z-propanol, was notseparated but was treated directly in the next dehydrochlorination step.

In the dehydrochlorination step, 40 g. of 40% sodium hydroxide solution,40 ml. of water, and 80 ml. of dimethyl sul-foxide were added to theabove reaction mixture which was then heated for a period of 2 (hourswhile main taining the temperature at 3085 C. The reaction mixture wascooled overnight and the sodium chloride formed in the reaction was thenremoved by filtration. Hexane was used to wash the residue on the filterpaper and the filtrate was separated; the oily layer was washed withsaturated sodium chloride solution and dried over sodiumsulfate-magnesium sulfiate and distilled to remove the hexane and toobtain as residue 106.3 g. of the glycidyl ether, 3 {1[1-(n-hexadecyloxy) 2-propoxy]-2-propoxy}-1,2- epoxypropane, which is alight yellow oil.

The sulfonate was formed by heating 62.2 g. (0.150 mole) of the glycidylether obtained above with 25.2 g. (0.20 mole) of sodium sulfite in amixture of 80 ml. each of water and ethanol. The mixture was heated at atem perature of 82 C. for -a period of 19 hours while maintaining the pHof the solution at 79 by the dropwise addition of 6 N hydrochloric acidas required. At the end of this time, the solution was dried bystripping oil water at reduced pressure while replacing it withisopropanol. The hot isopropanol solution was then filtered to removethe insoluble salts and the filtrate then cooled to permitcrystallization of the sulfonate product. The sulfionate product wasseparated by filtration and washed 3 times with isopropanol before beingdried in a vacuum oven at a temperature of 50 C. to obtain 55.2 g. ofthe sodium 3 {1 [1 (n-hex adecyl oxy) 2-propoxy]-2-propoxy}-2-hydroxy-l-prop anesulfonate which is a white solid.

Example 3 In this example, 1-'(1-isodecyloxypenta-2-propenoxy)-2-propanol Was prepared as in Example 1 from decyl alcohol andapproximately 6 moles of propylene oxide. This material was thenalkenoxylated in a second alkenoxylation step using 101.4 g. (0.20 mole)of the 1 ('1-is'odecyloxypenta-2-pnopenoxy)-2-propanol and 1 ml. ofboron trifluori'de-dietlhyl ether as a catalyst. The epichlorohydrin inan amount of 22.2 g. (0.24 mole) was added to the mixture at a rate soas to maintain the temperature at 85-95 C. After addition of theepichlorohydrin during a period of 30 minutes, the reaction mixture washeated for an additional 90 minutes while maintaining the temperature at80-85 C. The product,l-(l-isodecyloxyhexa-Z-propenoxy)-3-chloro-2-propanol, was not separatedfrom the reaction mixture but was treated in the dehydrochlori-nation toform the glycidyl ether.

In the 'dehydro-chlorination step, 40 g. (0.4 mole) of 40% sodiumhydroxide solution, 30 ml. of water and 60 ml. of dimethyl sulfoxidewere added to the reaction rnixture obtained above and the mixture washeated tor a period of 1 hour While maintaining the temperature at 8590C. At the end of this time, the sodium chloride fiormed in the reactionwas separated by filtration of the hot reaction mixture using hexane toimprove the separation. The oily layer was washed with saturated sodiumchloride solution and then dried over magnesium sulfate. The driedfiltrate was distilled to remove the hexane and to obtain 105.5 g. ofthe glycidyl ether, 3 (1-isodecyloxyhexa2-propenoxy)-l,2-epoxypropane,which is a light yellow oil.

The sulfonate was then prepared by heating 58.1 g. of the glycidyl ether(0.1 mole) with 18.9 g. of sodium sulfite (0.15 mole) using 100 ml. eachof water and ethanol. The heating of the reaction mixture was continuedfor a period of 4.75 hours while maintaining the temperature at 82 C.and using 6 N hydrochloric acid to maintain the pH in the range of 79.The sulfonate product was dried by stripping off the water at reducedpressure while replacing it with isopropanol. The sulionate product waspermitted to crystallize from the isoprcpanol solution by cooling[overnight and was recovered by filtration using a filter air. Thefiltrate Was concentrated to dryness under reduced pressure to obtain alight yellow oil in an amount lot 52.0 g. which is the desired sodium 3(1-isodecyloxyhexa-Q-propenoxy) -2 hydroxy- 1 -propanesulfon ate.

Example 4 1 l2. alcohols, marketed by Archer-Daniels-Midland Company asAdol 65, was used to prepare a glycidyl ether and sulfonate productthereof using approximately 1 mole each of butylene oxide andepichlorohydrin.

In the first alkenoxylation step, 258 g. (approximately 1.0 mole) ofAdol 65 was dried and then heated with 108 g. (15 moles) of hutyleneoxide using 3 ml. of boron trifluoride-diethyl ether as a catalyst. Theaddition of the butylene oxide was done at a temperature of 90 C. and

the exothermic heat of reaction caused the temperature to rise to 110 C.After completing the addition of the butylene oxide, the reactionmixture was heated for an additional 2 hours while maintaining thetemperature at 90 C. At the end of this time, the reaction mixtureobtained was filtered at C. using SuperFiltrol and Hytlo Supercel toimprove the filtration. The filter cake was washed with hexane and thefiltrate was aspirated at 150 C. to obtain 343 g. of the alkenoxylatedproduct.

The second alkenoxylation step was performed by adding 111 g. (1.20moles) of epichlorohydrin slowly over a period of 40 minutes to theproduct obtained in the first alkenoxylation step using 2.0 ml. of borontrifluoride-diethyl other as a catalyst. During the epichlorohydrinaddition, the temperature was maintained in the range of 8090 C. byexternal cooling and after the addition of the epichlorohydrin, thereaction mixture was heated for an additional 2 hours while maintainingthe temperature at -90 C.

The reaction product [from the second alkenoxylation step wasdehydrochlorinated directly using 150 g. (1.5 moles) of 40% sodiumhydroxide solution, 150 ml. of water, and ml. of dimethyl sulfioxide.This mixture was heated in :a period of 1 hour while maintaining thetemperature at 100-105 C. At the end of this time, the sodium chlorideformed in the reaction was removed by filtration, using hexane topromote separation. The

oily layer was washed with saturated sodium chloride solution and driedover magnesium sulfate then distilled to remove the hexane. The glycidylether product was obtained as an amber material in an amount of 346.2 g.

The sul-fonate product was formed by heating 62.6 g. of the glycidylother with 26.2 g. (0.20 mole) of sodium sulfite using 100 ml. each ofethanol and water. The reaction mixture was heated for a period of 9.25hours while maintaining the temperature at 82 C. and the pH at 79 by theperiodic addition of 6 N hydrochloric acid. The reaction mixture wasthen dried by stripping olf the water at reduced pressure whilereplacing it with isopropanol. The hot isopropanol solution was thenfiltered to remove salts and the filtrate permitted to cool. Thesulfonate product was recovered by evaporating the solution to drynessat 100 C./ 13 mm. to obtain 70.2 g. of the sulfonate which is a lightamber colored gum.

Example 5 dropwise to the Lorol No. 5 with cooling to maintain atemperature of 8590 C. After heating the mixture for a period of 1.5hours, the temperature was raised to 133 C. to distill over 81 .g. ofvolatile materials, principally methyl ethyl ketone. The product fromthe distillation is an ether alcohol derived from 2 moles of thehutylene oxide per mole of the original alcohol.

The product from the first alkenoxylation step was alkenoxylated in asecond step using 111 g. (1.2 moles) of epichlorohydrin and 1.0 ml. ofboron trifluoride- 13 diethyl ether as a catalyst. After addition of theepichlorohydrin the reaction mixture was heated for a period of 2 hourswhile maintaining the temperature at 8590 C. The product of thisreaction was the chlorohydrin substituted with an alkoxydialkenoxygroup.

The chlorohydrin obtained in the above step was then dehydrochlorinateddirectly by the addition thereto of 150 g. (1.5 moles) of 40% sodiumhydroxide, 100 ml. of water and 200 ml. ofdimethyl sulfoxide. Thismixture was heated at a temperature of 105110 C. for a period of 2hours. After this time the sodium chloride formed was separated byfiltration at an elevated temperature and the oily layer washed withsaturated sodium chloride solution, using hexane to effect theseparation. The wet oil was dried over magnesium sulfate-sodium sulfateand then distilled to remove the hexane, leaving 359 .g. of the glycidylether, which is a very faint yellow colored oil.

The sulfonate product was made by heating 81.0 g. (0.20 mole) of theglycidyl ether with 37.8 g. (0.30 mole) of sodium sulfite in 100 ml.each of water and ethanol. The mixture was heated for a period of 6.5hours While maintaining the temperature at 82-83 C. and using 6 Nhydrochloric acid, as needed, to maintain the pH at approximately 9. Atthe end of this time, the salts present in the reaction mixture wereremoved by filtration and the filtrate was dried by stripping off thewater at reduced pressure while replacing it with isopropanol. Theisopropanol was removed from the sulfonate solution thereof byevaporation at 130 C./ 13 mm. leaving 104.5 g. of the sodium sulfonate.This sulfonate is a translucent gum having a very light yellow color andis very viscous when cool.

Example 6 In this example, the sulfonate of the glycidyl ether,3-{1-[1-(dodecylphenoxy) 2 butoxy] 2 butoxy}-l,2- epoxypropane, wasprepared by heating 48.1 g. (0.10 mole) of the glycidyl other with 18.9g. (0.15 mole) of sodium sulfite using 100 ml. each of water andethanol.

reduced pressure at a temperature of 90 C.100 C. to leave 53.5 g. of thesodium 3-{1-[l-(dodecylphenoxy)-2- butoxy]-2butoxy}-2-hydroxy-l-propanesulfonate which is a light yellow gum.Example 7 In this example, the sulfonate of the glycidyl ether, 3 {l 7{1 [l-(dodecylphenoxy)-2-butoxy]-2-butoxy}-2- propoxy}-1,2-epoxypropane,was prepared from 57.7 g. (0.10 mole) of the glycidyl ether, 11.4 g. ofsodium metabisulfite, 30 ml. water, and 3 g. (0.03 mole) of 40% sodiumhydroxide. The above reactants were placed in a 300 ml. pressure bombwhich was pressure sealed and heated for approximately 2 hours at atemperature in the range of 175 C. to 195 C. At the end of this time,the reaction mixture was washed out of the bomb using 100 ml. ofethanol. The insoluble inorganic salts were removed by filtration. Thefiltrate was then dried by stripping oil the water at reduced pressurewhile replacing it with isopropanol. The isopropanol solution was againfiltered to remove insoluble salts. The filtrate was then concentratedto dryness under reducedpressure at a temperature of 100 C. to leave61.6 g. of the sodium 3 {1 {1 [l-(dodecylphenoxy)-2-butoxy}-2-butoxy}-2-propoxy}- 2-hydroxy-l-propanesulfonate which is a hard,

amber colored gum. Example 8 In this example, the sulfonate of theglycidyl ether, 3-(1-tridecyloxyhexa 2 propenoxy)-l,2-epoxypropane,

14 was prepared from 62.3 g. (0.10'mole) of the glycidyl ether, 3.0 .g.of 40% sodium hydroxide, 11.4 g. sodium metabisulfite, and 30 ml. water.The above reactants were placed in a 300 ml. pressure bomb which waspressure sealed and heated for approximately 2 hours at a temperature inthe range of 175 C. to 195 C. At the end of this time, the reactionproducts were removed from the bomb using ml. of ethanol. The ethanolsolution was dried by stripping oil the water at reduced pressure whilereplacing it with isopropanol. The insoluble salts were removed from theisopropanol solution by filtration. The filtrate was then concentratedto dryness under reduced pressure at elevated temperature to leave 60.4g. of sodium3-(l-tridecyloxyhexa-2-propenoxy)-2-hydr0xyl-propanesulfonate which is alight amber colored oil. Example 9 In this example, the stulfonate ofthe glycidyl ether, 3- l-tridecyloxytetra-Z-propenoxy)-l,2-epoxypropane, was prepared from 51.1 g. (0.10 mole) of the glycidylether, 11.4 g. of sodium metabisulfite, 3 g. of 40% sodium hydroxide,and 30 ml. of water. The above reactants were placed in [a 300 ml.pressure bomb which was pressure sealed and heated for approximately1.75 hours at a temperature in the range of C. to 195 C. At the end ofthis time, the reaction mixture was taken out of the bomb with 100 ml.of ethanol. The ethanol solution was dried by stripping oif the water atreduced pressure while replacing it with isopropanol. The insolublesalts were then removed from the isopropanol solution by filtration. Thefiltrate was concentrated to dryness under reduced pressure at elevatedtemperature to leave 57.1 g. of the sodium3-'(l-tridecycloxytetra-2-propenoxy)-2-hydroxy-lpropanesulfonate whichis an amber colored viscous gum.

Example 10 The wetting efficiencies of the sodium3-(1-isodecyloxyhexa-Z-propenoxy)-2-hydroxy-1 propanesulfonate ofExample 3 land the sodium sulfonate product of Example 5 were determinedby the Draves wetting test of the American Association of TextileChemists. The follow ing wetting times were measured at theconcentration shown:

Time in Seconds Compound Product of Example 3 1 Inst. 3. 4 8.2 27. 5+180 Product of Example 5 18.7 27.8 46.5 110. 5 +180 Compound:Dispersion number Sodium 3-[l-(n-hexadecyloxy)-2-propoxy] 2hydroxyl-propanesulfonate 20 Sodium 3-{1-[l-(n-hexadecyloxy) -2 propoxy]2- propoxy}-2-hydroxy-l-propanesulfonate 20 The sodium sulfonate productof Example 5 20 3-{ 1- 1- (dodecylphenoxy) -2-butoxy] -2 butyoxy}2-hydroxy-l-propanesulfonate 80 3-{1-{1-[1 (dodecylphenoxy) 2 butoxy] 2butoxy}-2-propoxy}-2 hydroxy 1 propanesulfonate 10 3-(l-tridecyloxyhexa-2-propenoxy)-2 hydroxy lpropanesulfonate 803(1-tridecyloxytetra-2-propenoxy)-2 hydroxy 1- propanesulfonate 80 1 5Example 12 The detergency properties of three of the sodium sulfonateproducts of this invention were measured by employing the methoddescribed by J. C. Harris [and E. L.

, Brown in the Journal of the American Oil Chemists Society, 27, 135143(1950). In this method, the detergency of the candidate compound iscompared with the detergency of Gardinol WA, a commercial detergentproduced by sulfating the mixture of alcohols, principally C obtained byhydrogenating coconut oil fatty acids. The following detersiveeificiencies were measured:

50 ppm. 300p.p.m Product water water 7 1 hardness hardness sodium3-[1-(n-hexadecyloxy)-2-propoxy1-2-hydroxy-l-propane-sulfonate 101 104sodium 3- {1-[1- (n-hexade eyloxy) -2-propoxy1-2- propoxyl-2-hydroxy-l-propanesulfonate 80 109 sodium3-(l-isodecyloxyhexa-2-propenoxy)'2- hydroXy-l-propanesullonate 133 11350 ppm. 300p.p.m. Product water water hardness h ardness sodium3-[1-(n-hexadecyloxy) -2-propoxy]-2-hydroxy-l-propanesulfonate 100 120sodium 3-{1-[1-(n-hexadecyloxy) 2-propoxy]-2- propoxy}-2-hydroXy-l-propanesulfonate 98 110 As surface active compositions, thealkali metal polyether-substituted 2-hydroxy-1-propanesulfonates of thisinvention comprise either the pure compounds or an admixture of the purecompounds with an adjuvant material or a diluent. Ordinarily, thecompounds of this invention are employed in surface active applicationsin a diluted form where the compound dissolved or suspended in someliquid medium such as water. The compounds of this invention can also beadmixed with adjuvant materials, particularly when used in soap orsynthetic detergent compositions, such as common inorganic builders ofthe type of carbonates, phosphates, silicates, and fillerssuch asstarch.

The new alkali metal sulfonates of this invention are particularlyuseful in soap and synthetic detergent comtions can be formed by mixingsmall proportions of soap with large proportions of the alkali metalsulfonates of this invention, usually the greatest value of soapcompositions of the present invention lie in compositions having lessthan by weight of the alkali metal sulfonate. In general, it ispreferred to incorporate in the soap composition about 5-50% by weightof the soap and the alkali metal sulfonate. Of course, other materialssuch as per fumes, fillers, and inorganic builders of the type such ascarbonates, phosphates and silicates, can also be present in thecompositions.

The soaps which are useful in the novel compositions of this inventionare the so-called water soluble soaps of the soap-making art and includesodium, potassium ammonium and amine salts of the higher fatty acids,that is, those having about 8 to 20 carbon atoms per molecule. Thesesoaps are normally prepared from such naturallyoccurring esters ascoconut oil, palm oil, olive oil, cottonseed oil, tung oil, corn oil,castor oil, soybean oil, wood fat, tallow, whale oil, menhaden oil, andthe like, as well as mixtures of these.

Reasonable variation and modification of the invention as described arepossible, the essence of which is that there have been provided (1)methods for preparing polyether derivatives of glyoidyl others from analcohol and an epoxyalkane, (2) methods for preparing alkali metalsulfonates of said polyether derivatives of glycidyl ethers, (3) saidalkali metal sulfonates of said polyether derivatives of tglycidylothers as new compounds, (4) said polyether derivatives of glycidylothers as new compounds, (5) said alkali metal sulfonate polyotherderivatives of glycidyl ethers as new surface active compositions, (6)detergent compositions comprising a sodium, potassium, or ammonium longchain fatty acid soap and said alkali metal sulfonate polyetherderivatives of glyoidyl ethers, and (7) methods for increasing the limesoap dispersion eificiency of soap-containing detergent compositions byincorporating an alkali metal sulfonate of a polyether derivative ofglyoidyl ether therein.

I claim:

1. 3 [1 (n hexadecyloxy) 2 propoxy] 1,2- epoxypropane.

2. 3 {1 [1 (n hexadecyloxy) propoxy] 2 propoxy}-1,2-epoxypropane.

3. 3 (1 isodecyloxyhexa 2 propenoxy) 1,2-

epoxypropane.

4. 3 {1 {1 [1 dode'cylphenoxy) 2 butoxy] 2- butoxy}-2-propoxy}-l,2-epoxypropane.

References Cited in the file of this patent UNITED STATES PATENTS

1. 3 - (1 - (N - HEXADECYLOXY) - 2 - PROPOXY) - 1,2EPOXYPROPANE.